CID 101676

Base Information

• Chemical Name: CID 101676
• CAS No.: 436-45-3
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Nikkaji Number: J11.389A
• Wikidata: Q104934975
• Mol file: 436-45-3.mol

Synonyms:geigerin

Chemical Property of CID 101676

Chemical Property:

• Vapor Pressure: 4.02E-11mmHg at 25°C
• Boiling Point: 477.5°Cat760mmHg
• Flash Point: 180.7°C
• PSA: 63.60000
• Density: 1.23g/cm³
• LogP: 1.47030
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 264.13615911
• Heavy Atom Count: 19
• Complexity: 479

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CC2C(C(C(=O)O2)C)C(C3=C(C(=O)CC13)C)O
• Isomeric SMILES: C[C@H]1C[C@@H]2[C@@H]([C@H](C(=O)O2)C)[C@@H](C3=C(C(=O)C[C@H]13)C)O

Technology Process of CID 101676

There total 20 articles about CID 101676 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C21H34O3Si → geigerin (436-45-3)

Guidance literature:

C₂₁H₃₄O₃Si; With 3,3-dimethyldioxirane; In acetone; at -90 ℃; for 0.166667h; Inert atmosphere;

With silica gel; at 23 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c3ob42049c

Reference yield:

C14H24O3Si → geigerin (436-45-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: quinoline; hydrogen; Lindlar's catalyst / ethyl acetate / 8 h / 23 °C / Inert atmosphere

2.1: camphor-10-sulfonic acid / dichloromethane; methanol / 12 h / 23 °C / Inert atmosphere

3.1: copper(l) iodide / diethyl ether / 0.5 h / 0 °C / Inert atmosphere

3.2: 1 h / 0 °C / Inert atmosphere

3.3: 12 h / 23 °C / Inert atmosphere

4.1: methanol / 10 h / 23 °C / Inert atmosphere

5.1: 1H-imidazole / dichloromethane / 10 h / 23 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 4 h / 0 - 23 °C / Inert atmosphere

8.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

8.2: 0.5 h / Inert atmosphere

9.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

10.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 12 h / 120 °C / Inert atmosphere

11.1: acetic anhydride; acetic acid; sodium acetate; sodium chromate(VI) / benzene / 12 h / 70 °C / Inert atmosphere

12.1: tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 14 h / 23 °C / Inert atmosphere

13.1: lithium perchlorate / dichloromethane / 5 h / 23 °C / Inert atmosphere

14.1: 3,3-dimethyldioxirane / acetone / 0.17 h / -90 °C / Inert atmosphere

14.2: 12 h / 23 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; quinoline; copper(l) iodide; n-butyllithium; sodium chromate(VI); Lindlar's catalyst; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; lithium perchlorate; 3,3-dimethyldioxirane; acetic anhydride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; acetone; toluene; benzene; 7.1: |Dess-Martin Oxidation;

DOI:10.1039/c3ob42049c

Reference yield:

C14H26O3Si → geigerin (436-45-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: camphor-10-sulfonic acid / dichloromethane; methanol / 12 h / 23 °C / Inert atmosphere

2.1: copper(l) iodide / diethyl ether / 0.5 h / 0 °C / Inert atmosphere

2.2: 1 h / 0 °C / Inert atmosphere

2.3: 12 h / 23 °C / Inert atmosphere

3.1: methanol / 10 h / 23 °C / Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 10 h / 23 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere

6.1: Dess-Martin periodane / dichloromethane / 4 h / 0 - 23 °C / Inert atmosphere

7.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

7.2: 0.5 h / Inert atmosphere

8.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 12 h / 120 °C / Inert atmosphere

10.1: acetic anhydride; acetic acid; sodium acetate; sodium chromate(VI) / benzene / 12 h / 70 °C / Inert atmosphere

11.1: tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 14 h / 23 °C / Inert atmosphere

12.1: lithium perchlorate / dichloromethane / 5 h / 23 °C / Inert atmosphere

13.1: 3,3-dimethyldioxirane / acetone / 0.17 h / -90 °C / Inert atmosphere

13.2: 12 h / 23 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; copper(l) iodide; n-butyllithium; sodium chromate(VI); camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium acetate; lithium perchlorate; 3,3-dimethyldioxirane; acetic anhydride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; toluene; benzene; 6.1: |Dess-Martin Oxidation;

DOI:10.1039/c3ob42049c

upstream raw materials:

(11R)-8β-hydroxy-6α-methanesulfonyloxy-3-oxo-1β-guai-4-en-12-oic acid-lactone

Refernces